AR074594A1 - DERIVATIVES OF 3- (3-PIRIMIDIN-2-IL-BENCIL) - (1,2,4) TRIAZOL (4,3-B) PYRIMIDINE - Google Patents

DERIVATIVES OF 3- (3-PIRIMIDIN-2-IL-BENCIL) - (1,2,4) TRIAZOL (4,3-B) PYRIMIDINE

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Publication number
AR074594A1
AR074594A1 ARP090104807A ARP090104807A AR074594A1 AR 074594 A1 AR074594 A1 AR 074594A1 AR P090104807 A ARP090104807 A AR P090104807A AR P090104807 A ARP090104807 A AR P090104807A AR 074594 A1 AR074594 A1 AR 074594A1
Authority
AR
Argentina
Prior art keywords
nhet
nhet1
hal
het1
nhconh
Prior art date
Application number
ARP090104807A
Other languages
Spanish (es)
Inventor
Oliver Schadt
Dieter Dorsch
Frank Stieber
Andree Blaukat
Original Assignee
Merck Patent Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Publication of AR074594A1 publication Critical patent/AR074594A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Los compuestos de la fórmula (1) en donde R1 es Ar, Het, A, CONHA, CONA2, OA, OHet, OAr, N(R5)2, NR5[C(R5)2]nHet, NR5[C(R5)2]nAr, COHet, SO2NHA o SO2NA2, R2 es H, A, Hal, OR5, N(R5)2, N=CR5N(R5)2, SR5, NO2, CN, COOR5, CON(R5)2, NR5COA, NR5SO2A, SO2N(R5)2, S(O)mA, Het, [C(R5)2]nN(R5)2, [C(R5)2]nHet, O[C(R5)2]nN(R5)2, O[C(R5)2]nHet, S[C(R5)2]nN(R5)2, S[C(R5)2]nHet, -NR5[C(R5)2]nN(R5)2, -NR5[C(R5)2]nHet, NHCON(R5)2, NHCONH[C(R5)2]nN(R5)2, NHCONH[C(R5)2]nHet, NHCO[C(R5)2]nN(R5)2, NHCO[C(R5)2]nHet, CON(R5)2, CONR5[C(R5)2]nN(R5)2, CONR5[C(R5)2]nHet, COHet, COA, O[C(R5)2]nNR5COZ, O[C(R5)2]nNR5COHet1, O[C(R5)2]nCyc[C(R5)2]nN(R5)2, O[C(R5)2]nCyc[C(R5)2]nOR5, O[C(R5)2]nCyc[C(R5)2]nHet1, O[C(R5)2]n-C(C)(C)-[C(R5)2]nN(R5)2, O[C(R5)2]nCR5(NR5)2COOR5, O[C(R5)2]nNR5CO[C(R5)2]nNR5COA, O[C(R5)2]nNR5COOA, O[C(R5)2]nCO-NR5-A, O[C(R5)2]nCO-NR5-[C(R5)2]nHet1, O[C(R5)2]nCONH2, O[C(R5)2]nCONHA, [C(R5)2]nCONA2, o O[C(R5)2]nCO-NR5-[C(R5)2]nN(R5)2; Z es CR5(NR5)2CR5(OR5)A, Cyc es cicloalquileno C3-7; R3, R3' son, en cada caso de modo independiente entre sí, H, F o A, juntos alquileno C2-5, R4 es H, A o Hal, R5 es H o A, A es alquilo no ramificado o ramificado C1-10, en donde 1-7 átomos de H pueden estar reemplazados por OH, F, Cl y/o Br, y/o en donde uno o dos grupos CH2 pueden estar reemplazados por O, NH, S, SO, SO2 y/o grupos CH=CH, o alquilo cíclico C3-7, Ar es fenilo, naftilo o bifenilo no sustituido o mono-, di- o trisustituido con Hal, A, OR5, N(R5)2, SR5, NO2, CN, COOR5, CON(R5)2, NR5COA, NR5SO2A, SO2N(R5)2, y/o S(O)mA, Het es un heterociclo mono-, bi- o tricíclico saturado, insaturado o aromático con 1 a 4 átomos de N, O y/o S, que puede no estar sustituido o que puede estar mono-, di- o trisustituido con Hal, A, OR5, N(R5)2, SR5, NO2, CN, COOR5, CON(R5)2, NR5COA, NR5SO2A, SO2N(R5)2, S(O)mA, CO-Het1, Het1, [C(R5)2]nN(R5)2, [C(R5)2]nHet1, O[C(R5)2]nN(R5)2, O[C(R5)2]nHet1, NHCOOA, NHCON(R5)2, NHCOO[C(R5)2]nN(R5)2, NHCOO[C(R5)2]nHet1, NHCONH[C(R5)2]nN(R5)2, NHCONH[C(R5)2]nHet, OCONH[C(R5)2]nN(R5)2, OCONH[C(R5)2]nHet1, CO-Het1, CHO, COA, =S, =NH, =NA y/u =O (oxígeno del carbonilo), Het1 es un heterociclo saturado monocíclico con 1 a 2 átomos de N y/u O, que puede estar mono- o disustituido con A, OA, OH, Hal y/u =O (oxígeno del carbonilo), Hal es F, Cl, Br o I; m es 0, 1 o 2, n es 1, 2, 3 o 4 así como sus sales, tautómeros y estereoisómeros farmacéuticamente aceptables, incluyendo sus mezclas en todas las proporciones. Son inhibidores de las tirosina quinasas, en especial de la Met-quinasa, y pueden utilizarse, por ejemplo, para el tratamiento de tumores. Composición farmacéutica y kit de compuesto.The compounds of the formula (1) wherein R1 is Ar, Het, A, CONHA, CONA2, OA, OHet, OAr, N (R5) 2, NR5 [C (R5) 2] nHet, NR5 [C (R5) 2] nAr, COHet, SO2NHA or SO2NA2, R2 is H, A, Hal, OR5, N (R5) 2, N = CR5N (R5) 2, SR5, NO2, CN, COOR5, CON (R5) 2, NR5COA, NR5SO2A, SO2N (R5) 2, S (O) mA, Het, [C (R5) 2] nN (R5) 2, [C (R5) 2] nHet, O [C (R5) 2] nN (R5) 2, O [C (R5) 2] nHet, S [C (R5) 2] nN (R5) 2, S [C (R5) 2] nHet, -NR5 [C (R5) 2] nN (R5) 2 , -NR5 [C (R5) 2] nHet, NHCON (R5) 2, NHCONH [C (R5) 2] nN (R5) 2, NHCONH [C (R5) 2] nHet, NHCO [C (R5) 2] nN (R5) 2, NHCO [C (R5) 2] nHet, CON (R5) 2, CONR5 [C (R5) 2] nN (R5) 2, CONR5 [C (R5) 2] nHet, COHet, COA, O [C (R5) 2] nNR5COZ, O [C (R5) 2] nNR5COHet1, O [C (R5) 2] nCyc [C (R5) 2] nN (R5) 2, O [C (R5) 2] nCyc [C (R5) 2] nOR5, O [C (R5) 2] nCyc [C (R5) 2] nHet1, O [C (R5) 2] nC (C) (C) - [C (R5) 2 ] nN (R5) 2, O [C (R5) 2] nCR5 (NR5) 2COOR5, O [C (R5) 2] nNR5CO [C (R5) 2] nNR5COA, O [C (R5) 2] nNR5COOA, O [C (R5) 2] nCO-NR5-A, O [C (R5) 2] nCO-NR5- [C (R5) 2] nHet1, O [C (R5) 2] nCONH2, O [C (R5) 2] nCONHA, [C (R5) 2] nCONA2, or O [C (R5) 2] nCO-NR5- [C (R5) 2] nN (R5) 2; Z is CR5 (NR5) 2CR5 (OR5) A, Cyc is C3-7 cycloalkylene; R3, R3 'are, in each case independently of each other, H, F or A, together C2-5 alkylene, R4 is H, A or Hal, R5 is H or A, A is unbranched or branched alkyl C1- 10, wherein 1-7 atoms of H may be replaced by OH, F, Cl and / or Br, and / or where one or two CH2 groups may be replaced by O, NH, S, SO, SO2 and / or groups CH = CH, or C3-7 cyclic alkyl, Ar is phenyl, naphthyl or unsubstituted or mono-, di- or trisubstituted with Hal, A, OR5, N (R5) 2, SR5, NO2, CN, COOR5, WITH (R5) 2, NR5COA, NR5SO2A, SO2N (R5) 2, and / or S (O) mA, Het is a saturated, unsaturated or aromatic mono-, bi- or tricyclic heterocycle with 1 to 4 atoms of N, O and / or S, which may not be substituted or which may be mono-, di- or trisubstituted with Hal, A, OR5, N (R5) 2, SR5, NO2, CN, COOR5, CON (R5) 2, NR5COA, NR5SO2A, SO2N (R5) 2, S (O) mA, CO-Het1, Het1, [C (R5) 2] nN (R5) 2, [C (R5) 2] nHet1, O [C (R5) 2] nN (R5) 2, O [C (R5) 2] nHet1, NHCOOA, NHCON (R5) 2, NHCOO [C (R5) 2] nN (R5) 2, NHCOO [C (R5) 2] nHet1, NHCONH [ C (R5) 2] nN (R5) 2, NHCONH [C (R5) 2] nHet, OCONH [C (R5) 2] nN (R5) 2, OCONH [C (R5) 2] nHet1, CO-Het1, CHO, COA, = S, = NH, = NA and / u = O ( carbonyl oxygen), Het1 is a monocyclic saturated heterocycle with 1 to 2 atoms of N and / or O, which may be mono- or disubstituted with A, OA, OH, Hal and / or = O (carbonyl oxygen), Hal is F, Cl, Br or I; m is 0, 1 or 2, n is 1, 2, 3 or 4 as well as its pharmaceutically acceptable salts, tautomers and stereoisomers, including mixtures in all proportions. They are inhibitors of tyrosine kinases, especially Met-kinase, and can be used, for example, for the treatment of tumors. Pharmaceutical composition and compound kit.

ARP090104807A 2008-12-18 2009-12-11 DERIVATIVES OF 3- (3-PIRIMIDIN-2-IL-BENCIL) - (1,2,4) TRIAZOL (4,3-B) PYRIMIDINE AR074594A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102008063667A DE102008063667A1 (en) 2008-12-18 2008-12-18 3- (3-pyrimidin-2-yl-benzyl) - ° [1,2,4] triazolo [4,3-b] pyrimidine derivatives

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AR074594A1 true AR074594A1 (en) 2011-01-26

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ARP090104807A AR074594A1 (en) 2008-12-18 2009-12-11 DERIVATIVES OF 3- (3-PIRIMIDIN-2-IL-BENCIL) - (1,2,4) TRIAZOL (4,3-B) PYRIMIDINE

Country Status (15)

Country Link
US (1) US8563561B2 (en)
EP (1) EP2358715B1 (en)
JP (1) JP5576395B2 (en)
KR (1) KR20110099742A (en)
CN (1) CN102256980A (en)
AR (1) AR074594A1 (en)
AU (1) AU2009328730B2 (en)
BR (1) BRPI0923085A2 (en)
CA (1) CA2747287C (en)
DE (1) DE102008063667A1 (en)
EA (1) EA018750B1 (en)
ES (1) ES2400112T3 (en)
MX (1) MX2011006424A (en)
WO (1) WO2010069441A1 (en)
ZA (1) ZA201105257B (en)

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Publication number Priority date Publication date Assignee Title
WO2011082271A2 (en) 2009-12-30 2011-07-07 Arqule, Inc. Substituted triazolo-pyrimidine compounds
US9796719B2 (en) * 2013-06-19 2017-10-24 Galapagos Nv Compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders
GB201321742D0 (en) * 2013-12-09 2014-01-22 Ucb Pharma Sa Therapeutic agents
GB201321745D0 (en) * 2013-12-09 2014-01-22 Ucb Pharma Sa Therapeutic agents

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Publication number Publication date
AU2009328730A1 (en) 2011-08-04
MX2011006424A (en) 2011-07-20
EA201100941A1 (en) 2012-01-30
CA2747287C (en) 2017-01-03
EA018750B1 (en) 2013-10-30
EP2358715B1 (en) 2012-12-26
AU2009328730B2 (en) 2015-12-17
CN102256980A (en) 2011-11-23
EP2358715A1 (en) 2011-08-24
BRPI0923085A2 (en) 2019-09-24
JP5576395B2 (en) 2014-08-20
DE102008063667A1 (en) 2010-07-01
ES2400112T3 (en) 2013-04-05
ZA201105257B (en) 2012-03-28
US20110257172A1 (en) 2011-10-20
US8563561B2 (en) 2013-10-22
JP2012512200A (en) 2012-05-31
KR20110099742A (en) 2011-09-08
CA2747287A1 (en) 2010-06-24
WO2010069441A1 (en) 2010-06-24

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